USRE12556E - Thilo - Google Patents
Thilo Download PDFInfo
- Publication number
- USRE12556E USRE12556E US RE12556 E USRE12556 E US RE12556E
- Authority
- US
- United States
- Prior art keywords
- acids
- acid
- blue
- manufacture
- sulfonic
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 210000002268 Wool Anatomy 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 150000001845 chromium compounds Chemical class 0.000 description 2
- 210000000496 Pancreas Anatomy 0.000 description 1
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
Definitions
- the invention relates to the manufacture of new-monoazo'dyestufis derived from 1- amido 2 acidyloxynaphthalenesulfonic acids and naphtholsulfonic acids,- according to v the general process described in an applica .cipitated by adding common salt;
- T ese new monoazo dyestuffs dissolve in water and in concentrated sulfuric acid with blue colorations and dye unmordanted wool Bo'rdeaux tints, becoming blue on treatment with chromium compoundsas for instance, potassium bichromate.
- the following example illustrates the manufacture of the new dyestuil: 23.9 kilos of 12- amidonaphtholr l-sulfonic acid are dis solved in two hundred liters of water with aid of twenty-nine kilos of sodadyeof thirty per cent. more and acct li-zed by means of eleven kilos of acetic anhy id at a temperature be: low 0 eentigrade, while good stirring is maintained.
- sulfonic acids of l-2 amidonaphthole as, for instance, 1 2-amidonaphthol-fi-sulfonic acid, 1 2an1idonaphtholl ddisulfonic acid,. 1-2- amidonaphthol 3 6 disulfonic acidmay also be employed.
Description
,THEELO'KRGEBQER, osrsassn swi uNrrnn srArEs PATENT OFFICE...
Teen-LAND; ASSlGNOR TO THE stem or SQCIETY (ll QHEM ICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND.
lic- 80B,415, dated December 5, IQQE.
To alt whom it may concern.-
Be it known that 1, Tune Knonenn, chem-. ist and doctor of Duke of SaKe-Altenburg, and a resident of ;Basel, Switzerland, have invented new and V useful Improvements in the Manufacture of Monoazo Dyestuffs, of which the following is a full, clear, and complete specification.
The invention relates to the manufacture of new-monoazo'dyestufis derived from 1- amido 2 acidyloxynaphthalenesulfonic acids and naphtholsulfonic acids,- according to v the general process described in an applica .cipitated by adding common salt;
tion for Letters Patent executed by me and Carl Jagerspaeher, Serial No. 261,897, dated May 23, 1905.
T ese new monoazo dyestuffs dissolve in water and in concentrated sulfuric acid with blue colorations and dye unmordanted wool Bo'rdeaux tints, becoming blue on treatment with chromium compoundsas for instance, potassium bichromate.
The following example illustrates the manufacture of the new dyestuil: 23.9 kilos of 12- amidonaphtholr l-sulfonic acid are dis solved in two hundred liters of water with aid of twenty-nine kilos of sodadyeof thirty per cent. more and acct li-zed by means of eleven kilos of acetic anhy id at a temperature be: low 0 eentigrade, while good stirring is maintained. After a few minutes there are added to the solution, whichlshould have neutral or feebly alkaline reaction, seven kilos of solidlsodium nitrite, and the whole is acidified at 0 centigrade byaddingall at .more uickly on heating to centigrade, a
pure-h ue dyestufi -isobtained, which is presolves in water and'in concentrated" sulfuric acid with blue colorations and dyes wool in acid-baths Bordeaux tints, which become blue by subsequent-treatment withphro mium compounds. By replacingin this example 1-5-naphtholsulfonic acidby the 'isomeric ll naphtholsulfonic' acid the obtained dyestufi of analogous. properties becomes philosophy, a subject of the owimmediately into a" It disewe Az'o eve AN Pancreas OF M KING same.
Specification of Reissued. Letters Patent. Reissued Nov. 13,1906.
Application for reissue filed August 1, 1906. sa e No. 328,319.
more reddish blue by its treatment on wool with chromium compounds.
sulfonic acids of l-2 amidonaphthole as, for instance, 1 2-amidonaphthol-fi-sulfonic acid, 1 2an1idonaphtholl ddisulfonic acid,. 1-2- amidonaphthol 3 6 disulfonic acidmay also be employed.
' What I claim isl. The process forthe manufacture of mo- Instead of he l-2+amidonaphthol- 4sul ionic acid mentioned in the example, other noazo dyestufis by acidylizing sulfonic acids Q of l2-amidonaphthol in the hydroxyl group, then diazotizing the so-obtained amido-2 acidyloxynaphthalenesulfonic acids and comnaphtholsulfonic acids.
bimng the resultingv diazo compounds with 2. The process for the manufacture of mo noazo dyestuffs which process consists in acetylizing sulfonic acids of 1-2-amidonaph thol in the hydroxyl group, then diazotizing lenesulfonic acids and combining the resulting diazo compounds with naphtholsulfonicv acids.
3(The rocess for the manufacture of a the so-obt ained Lamido 2 -'acetoxynaphtha+ -n1onoazo yestufl, which process consists in acetylizing 1 2 amidonaphth'ol 4 sulfonic acid-in the hydroxyl group, then diazotizing the so-obtained l-amido-2-acetoxynaphtha' lene-e-sulfonic acid and combining the re.-
sulfonic acid.
4. As new products the monoazo dyestuffs,
derived from sulfonic acidsof 1-2 -aniidona hthol and naphtholsulfonic acids, which (yer stuff's yield blue solutions in water, and ye unmordantedwool inBordeaux shades, be-
coming bluev on treatment with chromium compounds. r i V 5. As a new productthe monoaze dyestuff, derived from J-Z-amidonaphthol--sulwhich dyestuff yields blue solutionsin water and in concentrated sulfuric acid and dyes ,Ammn Rims.
'umnordant'e'd wool in Bordeaux shades besuiting diazo compound with 1-5 naphth01- fonic acid and 1-5-naphtholsullonic acid,
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Family
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